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WO2014050690A1 - Produit semi-durci, produit durci, procédé de fabrication de produit semi-durci, procédé de fabrication de produit durci, élément optique, composition de résine durcissable et composé - Google Patents

Produit semi-durci, produit durci, procédé de fabrication de produit semi-durci, procédé de fabrication de produit durci, élément optique, composition de résine durcissable et composé Download PDF

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WO2014050690A1
WO2014050690A1 PCT/JP2013/075283 JP2013075283W WO2014050690A1 WO 2014050690 A1 WO2014050690 A1 WO 2014050690A1 JP 2013075283 W JP2013075283 W JP 2013075283W WO 2014050690 A1 WO2014050690 A1 WO 2014050690A1
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independently
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Japanese (ja)
Inventor
あゆみ 染谷
芳沢　昌孝
大林　達彦
寛之 内藤
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Fujifilm Corp
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Fujifilm Corp
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Application filed by Fujifilm Corp filed Critical Fujifilm Corp
Priority to CN201380050345.1A priority Critical patent/CN104684946B/zh
Publication of WO2014050690A1 publication Critical patent/WO2014050690A1/fr
Priority to US14/668,474 priority patent/US9334352B2/en
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    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
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    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
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    • C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
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    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/26—Nitrogen
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/34—Monomers containing two or more unsaturated aliphatic radicals
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
    • C09D125/02—Homopolymers or copolymers of hydrocarbons
    • C09D125/16—Homopolymers or copolymers of alkyl-substituted styrenes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety

Definitions

  • the present invention relates to a semi-cured product, a cured product, a production method thereof, an optical component, a cured resin composition, and a compound.
  • Imaging modules are used in cameras, video cameras, camera-equipped mobile phones, videophones, camera-equipped doorphones, and the like.
  • the optical system used in this imaging module is particularly required to be downsized.
  • the chromatic aberration of the optical system becomes a big problem.
  • Conventionally used glass as an optical system material is capable of realizing various required optical properties and is excellent in environmental resistance, but has a problem of poor workability.
  • resin cured products that are cheaper than glass materials and excellent in workability have been used for optical components.
  • a method of changing various properties after curing by adding various additives to the cured resin composition is known.
  • chromatic aberration has been achieved by making the material composition highly dispersed by reducing the Abbe number with a high refractive index. It has been known that the correction can be performed.
  • Patent Document 1 describes a (meth) acrylate compound having a 9,9-bisphenylfluorene skeleton, which describes that a composition having a high refractive index that can be used as an optical material can be provided.
  • Patent Document 2 describes a method for producing alcohols, epoxies, and (meth) acrylates having a fluorene skeleton, and describes that a compound with significantly less coloring can be provided.
  • Patent Document 2 discloses (meth) acrylates having a 9,9-bisphenylfluorene skeleton and (meth) acrylates having a 9,9-bisnaphthylfluorene skeleton.
  • Patent Documents 1 and 2 do not describe a method for reducing the Abbe number of a cured product when a monomer having a fluorene skeleton is used.
  • Patent Document 3 the generation of burrs during molding is suppressed by semi-curing a composition containing a (meth) acrylate monomer having an alicyclic structure and a non-conjugated vinylidene group-containing compound. It is described that the rate increases.
  • Patent Document 3 has no description suggesting the use of a monomer having an aromatic ring structure. Further, Patent Document 3 does not describe a method for reducing the Abbe number of the cured product.
  • Patent Document 4 describes that an optical material having a small Abbe number can be provided by using a polyester polymer using an alcohol having a fluorene skeleton as one of the copolymerization components.
  • the present inventors produced a lens using a composition containing 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] fluorene diacrylate described in Example 28 of Patent Document 2.
  • Example 1 which semi-cures the composition containing the (meth) acrylate monomer having an alicyclic structure and a non-conjugated vinylidene group-containing compound of Patent Document 3 was re-examined, the Abbe number was very high and a further low Abbe number It turned out that it is required.
  • the present invention aims to solve the above problems. That is, the problem to be solved by the present invention is to provide a cured resin composition capable of producing a cured product having a low Abbe number by suppressing the occurrence of burrs during molding.
  • the present inventors have used a non-conjugated vinylidene group-containing compound described in Patent Document 3 using a monomer containing a 9,9-bisphenylfluorene skeleton, which is the compound (19) of Patent Document 1. Further, when a lens was produced using the added composition, it was found that the Abbe number was still high and a further lower Abbe number was required. Therefore, the present inventors have a curing comprising a monomer having a specific structure having at least one aromatic fused ring skeleton and a plurality of polymerizable groups, and a non-conjugated vinylidene group-containing compound having a specific structure.
  • a cured resin composition comprising: General formula (1) (In the general formula (1), Ar 1 to Ar 4 each independently represents an aryl group or a heteroaryl group which may have a substituent, and at least one of Ar 1 to Ar 4 has a substituent. an aromatic fused ring group which may have two or more of Ar 1 ⁇ Ar 4 contains a substituent having a polymerizable group.
  • a and b each independently represents an integer of 1 to 5
  • c and d each independently represents an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent
  • e , F, g and h each independently represents an integer of 0 or more
  • the upper limit values of e, f, g and h are a, b, c or from the number of substituents each of Ar 11 to Ar 14 can have. With a value obtained by subtracting d That.
  • Ar 11 to Ar 14 each independently represents an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line, and at least one of Ar 11 to Ar 14 is surrounded by a broken line.
  • An aromatic condensed ring group containing a benzene ring as one of the condensed rings L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom, and R 5 to R 8 are each independently a single bond or An alkylene group which may have a substituent; L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond; and R 9 to R 12 each independently represents a hydrogen atom or methyl .a and b represents a group each independently represents an integer of 1-5, the .R 1 ⁇ R 4 each independently represents a substituent c and d representing each independently an integer of 0 to 5 And, e, f, g and h each independently represent an integer of 0 or more, e, f, g and h a from the number of substituents upper limit capable of Ar 11 ⁇ Ar 14 have each, b , C or d, provided that when Ar 11 to Ar 14 are each independently an
  • the condensed ring-containing compound represented by the general formula (1) is represented by the following general formula (5). It is preferable.
  • General formula (5) (In the general formula (5), Ar 11 and Ar 12 each independently represent an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line.
  • Ar 13 and Ar 14 each independently represent a benzene surrounded by a broken line.
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently single bond, an ester bond, represents a thioester or amide bond
  • a and b representing the R 9 ⁇ R 12 are each independently a hydrogen atom or a methyl group It represents an integer of respectively independently 1 ⁇ 5, c and d each independently .
  • R 1 ⁇ R 4 representing a is each independently an integer of 0 to 5 represent a substituent
  • e, f, g and h are Each independently represents an integer of 0 or more, the upper limit values of e and f are 5-a and 5-
  • Ar 13 and Ar 14 are each independently an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings.
  • the structure enclosed in parentheses and R 3 and R 4 may be each independently substituted with a benzene ring enclosed with a broken line, or may be substituted with a ring other than the benzene ring enclosed with a broken line.
  • the condensed ring-containing compound represented by the general formula (1) is represented by the following general formulas (6) to (9). It is preferable that it is represented by either.
  • General formula (6) General formula (7)
  • General formula (8) General formula (9)
  • Ar 11 and Ar 12 each independently represent an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line.
  • L 1 to L 4 each independently represents a single bond.
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represent a single bond, an ester bond
  • R 9 to R 12 each independently represents a hydrogen atom or a methyl group
  • a and b each independently represent an integer of 1 to 5
  • c and d each independently represent 0 to 5
  • R 1 to R 4 each independently represents a substituent
  • e, f, g, and h each independently represent an integer of 0 or more, provided that Ar 11 and Ar 12 are each independently In the case of an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings, a and b parenthesized structures and R 1 and R 2 are each independently surrounded by a broken line.
  • the condensed ring-containing compounds represented by the general formulas (6) to (9) are represented by the following general formulas (6A), (7A), (8A), It is preferably represented by any one of (9A), (6B), (7B), (8B) and (9B).
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • R 9 to R 12 each independently represent a hydrogen atom Or a methyl group
  • a and b each independently represent an integer of 1 to 5
  • c and d each independently represent an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent, e, f, g and h each independently represent an integer of 0 or more.
  • General formula (6B) General formula (7B)
  • General formula (8B) General formula (9B) (Formula (6B), represent (7B), (8B) and (9B) in, Ar 11 and Ar 12 aryl or heteroaryl group containing a benzene ring surrounded by a broken line are each independently, Ar 11 and At least one of Ar 12 is an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings
  • L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • 9 to R 12 each independently represents a hydrogen
  • the cured resin composition according to any one of [3] to [7] has the general formulas (4) to (9), (6A), (7A), (8A), and (9A). , (6B), (7B), (8B) and (9B), L 1 to L 4 each independently represents an oxygen atom or a sulfur atom, and L 5 to L 8 is independently an ester bond, represents a thioester bond or an amide bond, preferably represents an R 5 ⁇ R 8 is an alkylene group which may independently have a substituent.
  • the cured resin composition according to any one of [1] to [11] preferably contains a thermal radical polymerization initiator and a photo radical polymerization initiator.
  • the cured resin composition according to any one of [1] to [12] further includes a monofunctional (meth) acrylate monomer, and the condensed ring-containing compound represented by the general formula (1) On the other hand, the monofunctional (meth) acrylate monomer is preferably contained in an amount of 10 to 80% by mass.
  • a method for producing a semi-cured product comprising a step of curing the cured resin composition according to any one of [1] to [13].
  • the method for producing a semi-cured product according to [14] preferably includes a step of irradiating the cured resin composition with light.
  • the cured resin composition is irradiated with light, and a complex viscosity at 25 ° C. and a frequency of 10 Hz is 10 5 to 10 8. It is preferable to form a semi-cured product of mPa ⁇ s.
  • a semi-cured product produced by the method for producing a semi-cured product according to any one of [14] to [16] is placed in a mold, subjected to pressure deformation, heated and thermally polymerized to be cured. The manufacturing method of the hardened
  • a compound represented by the following general formula (5) General formula (5) (In the general formula (5), Ar 11 and Ar 12 each independently represent an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line. Ar 13 and Ar 14 each independently represent a benzene surrounded by a broken line.
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently single bond, an ester bond, represents a thioester or amide bond
  • a and b representing the R 9 ⁇ R 12 are each independently a hydrogen atom or a methyl group It represents an integer of respectively independently 1 ⁇ 5, c and d each independently .
  • R 1 ⁇ R 4 representing a is each independently an integer of 0 to 5 represent a substituent
  • e, f, g and h are Each independently represents an integer of 0 or more, the upper limit values of e and f are 5-a and 5-
  • Ar 13 and Ar 14 are each independently an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings.
  • the structure enclosed in parentheses and R 3 and R 4 may be each independently substituted with a benzene ring enclosed with a broken line, or may be substituted with a ring other than the benzene ring enclosed with a broken line.
  • the compound according to [22] includes an aromatic hydrocarbon group having 6 to 10 carbon atoms including a benzene ring in which Ar 13 and Ar 14 are each independently surrounded by a broken line in the general formula (5). It is preferable to represent.
  • the compound represented by the general formula (5) is preferably represented by any one of the following general formulas (6) to (9).
  • General formula (6) General formula (7)
  • General formula (8) General formula (9)
  • Ar 11 and Ar 12 each independently represent an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line.
  • L 1 to L 4 each independently represents a single bond.
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represent a single bond, an ester bond
  • R 9 to R 12 each independently represents a hydrogen atom or a methyl group
  • a and b each independently represent an integer of 1 to 5
  • c and d each independently represent 0 to 5
  • R 1 to R 4 each independently represents a substituent
  • e, f, g, and h each independently represent an integer of 0 or more, provided that Ar 11 and Ar 12 are each independently In the case of an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings, a and b parenthesized structures and R 1 and R 2 are each independently surrounded by a broken line.
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • R 9 to R 12 each independently represent a hydrogen atom Or a methyl group
  • a and b each independently represent an integer of 1 to 5
  • c and d each independently represent an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent, e, f, g and h each independently represent an integer of 0 or more.
  • General formula (6B) General formula (7B)
  • General formula (8B) General formula (9B) (Formula (6B), represent (7B), (8B) and (9B) in, Ar 11 and Ar 12 aryl or heteroaryl group containing a benzene ring surrounded by a broken line are each independently, Ar 11 and At least one of Ar 12 is an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings
  • L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • 9 to R 12 each independently represents a hydrogen
  • the compound according to any one of [22] to [25] is the compound represented by the general formulas (5) to (9) and (6A), (7A), (8A), (9A), (6B ), (7B), (8B) and (9B), L 1 to L 4 each independently represents an oxygen atom or a sulfur atom, and L 5 to L 8 each independently represents an ester bond, a thioester bond or an amide bond. It is preferable that R 5 to R 8 each independently represents an alkylene group which may have a substituent.
  • the compound according to any one of [22] to [26] is a compound of the general formulas (5) to (9) and (6A), (7A), (8A), (9A), (6B ), (7B), (8B) and (9B), it is preferable that both c and d are 0.
  • the compound represented by the general formula (5) is preferably any one of the following Xa-4 to Xa-15: .
  • a cured resin composition that can suppress the generation of burrs during molding and can produce a cured product having a low Abbe number.
  • 2 is a 1 H-NMR chart of a condensed ring-containing compound Xa-4.
  • 2 is a 1 H-NMR chart of a condensed ring-containing compound Xa-5.
  • 2 is a 1 H-NMR chart of a condensed ring-containing compound Xa-6.
  • 2 is a 1 H-NMR chart of a condensed ring-containing compound Xa-8.
  • 2 is a 1 H-NMR chart of a condensed ring-containing compound Xa-10.
  • a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the cured resin composition of the present invention includes a condensed ring-containing compound represented by the following general formula (1), a non-conjugated vinylidene group-containing compound represented by the following general formula (2), and a thermal or photo radical polymerization initiator. And at least one of the above.
  • General formula (1) Ar 1 to Ar 4 each independently represents an aryl group or a heteroaryl group which may have a substituent, and at least one of Ar 1 to Ar 4 has a substituent.
  • an aromatic fused ring group which may have two or more of Ar 1 ⁇ Ar 4 contains a substituent having a polymerizable group. Further, Ar 1 ⁇ Ar 4 may be linked.
  • the condensed ring-containing compound represented by the general formula (1) is preferable from the viewpoint of remarkably improving mold releasability.
  • R 21 to R 26 each independently represents a substituent, and at least one of R 21 to R 26 forms a ring, or at least two of them combine with each other to form a ring. is doing.
  • the cured resin composition of the present invention can suppress the generation of burrs during molding and can produce a cured product having a low Abbe number.
  • the condensed ring-containing compound represented by the general formula (1) having at least one aromatic condensed ring skeleton and having a plurality of polymerizable groups is used as a monomer,
  • the Abbe number can be lowered, and the deformability of the semi-cured product is imparted by controlling the three-dimensional structure by chain transfer during the polymerization of the non-conjugated vinylidene group-containing compound monomer represented by the general formula (2).
  • the generation of burrs can be suppressed and the above-described problems can be solved.
  • an optical component having a low Abbe number can be obtained as described in Quarterly Chemical Review (No. 39), Refractive Index Control of Transparent Polymers, pages 174 to 177 of the Chemical Society of Japan.
  • a monomer having an aromatic ring has absorption in the vicinity of 250 to 300 nm, and therefore the Abbe number is smaller than that in the case of using an aliphatic monomer having absorption in the vicinity of 120 to 200 nm.
  • the condensed ring-containing compound represented by the general formula (1) has a long conjugated system. The longer the conjugated system is extended, the lower the Abbe number and the higher the refractive index. Note that a long conjugated system may absorb visible light.
  • mold releasability when producing a cured product using the cured resin composition can be enhanced.
  • (meth) acrylate represents acrylate and methacrylate
  • (meth) acryl represents acryl and methacryl
  • (meth) acryloyl represents acryloyl and methacryloyl.
  • monomer and “monomer” are synonymous.
  • the monomer in the present invention is distinguished from an oligomer and a polymer, and refers to a compound having a weight average molecular weight of 1,000 or less.
  • Ar 1 to Ar 4 each independently represents an aryl group or a heteroaryl group which may have a substituent, and at least one of Ar 1 to Ar 4 has a substituent.
  • An aromatic fused ring group which may be substituted, and two or more of Ar 1 to Ar 4 contain a substituent having a polymerizable group.
  • Ar 1 to Ar 4 may be linked.
  • the aryl group which may have a substituent represented by Ar 1 to Ar 4 is preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 14 carbon atoms, An aryl group having a number of 6 to 10 is particularly preferable.
  • the heteroaryl group which may have a substituent represented by Ar 1 to Ar 4 is preferably a heteroaryl group having 4 to 12 ring members, and more preferably a heteroaryl group having 6 to 10 ring members.
  • a heteroaryl group having 9 ring members is particularly preferable.
  • Examples of the hetero atom constituting the heteroaryl group which may have a substituent represented by Ar 1 to Ar 4 include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • Ar 1 to Ar 4 are preferably each independently an aryl group which may have a substituent.
  • the aromatic condensed ring group which may have a substituent represented by Ar 1 to Ar 4 is preferably an aryl group having 9 to 12 carbon atoms or a heteroaryl group having 4 to 12 ring members, and has 9 carbon atoms. It is more preferably an aryl group having ⁇ 10 or a heteroaryl group having 6 to 10 ring members, and particularly a naphthyl group or a heteroaryl group having 9 ring members is particularly preferable from the viewpoint of suppressing coloring without excessively extending the conjugated system. A naphthyl group is more preferable, and a ⁇ -naphthyl group is even more particularly preferable.
  • At least one of Ar 1 to Ar 4 is an aromatic condensed ring group that may have a substituent, and one to three may be an aromatic condensed ring group that may have a substituent.
  • 1 or 2 is an aromatic condensed ring group which may have a substituent.
  • a polymerizable group capable of radical polymerization or cationic polymerization hereinafter referred to as a radical polymerizable group and a cationic polymerizable group, respectively) is preferable.
  • radical polymerizable group a generally known radical polymerizable group can be used, and a polymerizable group having an ethylenically unsaturated bond capable of radical polymerization can be mentioned as a preferred one.
  • examples thereof include a vinyl group and a (meth) acryloyloxy group.
  • a (meth) acryloyloxy group is preferable, and an acryloyloxy group is more preferable.
  • cationic polymerizable group generally known cationic polymerizable groups can be used.
  • examples include groups. Among these, alicyclic ether groups and vinyloxy groups are preferable, and epoxy groups, oxetanyl groups, and vinyloxy groups are particularly preferable.
  • the polymerizable group contained in the substituent contained in Ar 1 to Ar 4 is preferably a radical polymerizable group.
  • Two or more of Ar 1 ⁇ Ar 4 includes a substituent having a polymerizable group, preferably contains a substituent 2-4 of Ar 1 ⁇ Ar 4 has a polymerizable group, Ar 1 ⁇ Ar more preferably comprising a substituent having 2 or 3 polymerizable groups of 4, and particularly preferably contains a substituent having two polymerizable groups of Ar 1 ⁇ Ar 4.
  • Ar 1 to Ar 4 may be linked.
  • the ring to be formed when Ar 1 to Ar 4 are connected is preferably an alicyclic ring.
  • Examples of the linking group when Ar 1 to Ar 4 are linked include a single bond and —O—.
  • a single bond is preferable.
  • the number of ring members (not the entire ring) is preferably 5 or 6, and more preferably 5.
  • Ar 1 to Ar 4 it is preferable that two adjacent ones of Ar 1 to Ar 4 are connected, more preferably Ar 3 and Ar 4 are connected, and Ar 1 to Ar 4 are connected. it is particularly preferred that only Ar 3 and Ar 4 of Ar 4 are linked.
  • Ar 11 to Ar 14 each independently represents an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line, and at least one of Ar 11 to Ar 14 is surrounded by a broken line.
  • X 1 to X 4 each independently represents a substituent having a polymerizable group, and the carbon atom in the substituent may be substituted with a hetero atom.
  • a and b each independently represents an integer of 1 to 5, and c and d each independently represents an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent, e, f, g and h each independently represent an integer of 0 or more, and the upper limit values of e, f, g and h are Ar 11 to Ar 14 respectively. This is a value obtained by subtracting a, b, c or d from the number of substituents which can be possessed.
  • Ar 11 to Ar 14 are each independently an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings
  • X 1 to X 4 and R 1 to R 4 are each independently It may be substituted with a benzene ring surrounded by a broken line, or may be substituted with a ring other than the benzene ring surrounded by a broken line.
  • a preferable range of the aryl group including a benzene ring surrounded by a broken line represented by Ar 11 to Ar 14 has a substituent represented by Ar 1 to Ar 4 in the general formula (1). This is the same as the preferred range of the aryl group that may be present.
  • the heteroaryl group containing a benzene ring surrounded by a broken line represented by Ar 11 to Ar 14 is preferably a heteroaryl group having 9 to 14 ring members, and having 9 to 10 ring members. A heteroaryl group is more preferable, and a heteroaryl group having 9 ring members is particularly preferable.
  • the hetero atom constituting the heteroaryl group optionally having a substituent represented by Ar 11 to Ar 14 includes a hetero atom constituting the heteroaryl group represented by Ar 1 to Ar 4 in the general formula (1) It is the same.
  • Ar 11 to Ar 14 are preferably each independently an aryl group containing a benzene ring surrounded by a broken line.
  • a preferred range of the aromatic fused ring group containing a benzene ring surrounded by a broken line represented by Ar 11 to Ar 14 as one of the condensed rings is Ar 1 to Ar in the general formula (1). This is the same as the preferred range of the aromatic condensed ring group which may have a substituent represented by 4 .
  • Ar 11 and Ar 12 each independently represent an aromatic hydrocarbon group having 6 to 10 carbon atoms (including a benzene ring surrounded by a broken line) from the viewpoint of reducing the Abbe number.
  • Ar 13 and Ar 14 each independently represent an aromatic hydrocarbon group having 6 to 10 carbon atoms (including a benzene ring surrounded by a broken line) from the viewpoint of reducing the Abbe number. More preferably, at least one of Ar 13 and Ar 14 represents an aromatic hydrocarbon group having 10 carbon atoms (including a benzene ring surrounded by a broken line).
  • X 1 to X 4 each independently represent a substituent having a polymerizable group, and the carbon atom in the substituent may be substituted with a hetero atom.
  • the substituent having a polymerizable group represented by X 1 to X 4 is not particularly limited, but is preferably an aliphatic group having a polymerizable group.
  • the aliphatic group having a polymerizable group represented by X 1 to X 4 is not particularly limited, but is preferably an alkylene group having 1 to 12 carbon atoms other than the polymerizable group, and having 2 to 10 carbon atoms. An aliphatic group is more preferable, and an alkylene group having 2 to 5 carbon atoms is particularly preferable.
  • the aliphatic group having a polymerizable group represented by X 1 to X 4 when the aliphatic group is substituted with a heteroatom, it is substituted with —NR— (R is a substituent), an oxygen atom, or a sulfur atom.
  • R is a substituent
  • the non-adjacent —CH 2 — in the aliphatic group is more preferably substituted with an oxygen atom or a sulfur atom, and the non-adjacent —CH 2 — in the aliphatic group is Particularly preferred is substitution with an oxygen atom.
  • the aliphatic group having a polymerizable group represented by X 1 to X 4 is preferably substituted at one or two sites by a hetero atom, more preferably substituted at one site by a hetero atom, Ar 11 to Ar It is particularly preferable that one position adjacent to the aryl group containing a benzene ring surrounded by a broken line represented by 14 is substituted with a hetero atom.
  • the preferred range of the polymerizable group contained in the aliphatic group having the polymerizable group represented by X 1 to X 4 is the preferred range of the polymerizable group contained in the substituent contained in Ar 1 to Ar 4 in the general formula (1). It is the same.
  • X 1 to X 4 are each independently a benzene ring surrounded by a broken line. Even if it is substituted, it may be substituted with a ring other than the benzene ring surrounded by a broken line.
  • a and b each independently represent an integer of 1 to 5, preferably 1 or 2, and more preferably a and b are both 1.
  • c and d each independently represent an integer of 0 to 5, preferably 0 or 1, and more preferably c and d are both 0.
  • R 1 to R 4 each independently represents a substituent.
  • the substituent represented by R 1 to R 4 is not particularly limited, and examples thereof include halogen atoms, halogenated alkyl groups, alkyl groups, alkenyl groups, acyl groups, hydroxyl groups, hydroxyalkyl groups, alkoxy groups, aryl groups, hetero groups An aryl group, an alicyclic group, etc. can be mentioned.
  • the substituent represented by R 1 to R 4 is preferably an alkyl group, an alkoxy group or an aryl group, more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a phenyl group.
  • R 1 to R 4 are each independently It may be substituted with a benzene ring surrounded by a broken line, or may be substituted with a ring other than the benzene ring surrounded by a broken line.
  • e, f, g and h each independently represent an integer of 0 or more, and the upper limit values of e, f, g and h can each be a substituent which Ar 11 to Ar 14 can have.
  • the value obtained by subtracting a, b, c, or d from the number of. e, f, g and h are preferably each independently 0 to 8, more preferably 0 to 2, and particularly preferably 0.
  • Ar 11 to Ar 14 are each an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings, e, f, g and h are preferably 0 or 1. It is more preferable that
  • the condensed ring-containing compound represented by the general formula (1) is preferably represented by the following general formula (4).
  • General formula (4)
  • Ar 11 to Ar 14 each independently represents an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line, and at least one of Ar 11 to Ar 14 is surrounded by a broken line
  • L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • R 9 to R 12 each independently represents a hydrogen atom or a methyl group.
  • a and b each independently represents an integer of 1 to 5, and c and d each independently represents an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent, e, f, g and h each independently represent an integer of 0 or more, and the upper limit values of e, f, g and h are Ar 11 to Ar 14 respectively. This is a value obtained by subtracting a, b, c or d from the number of substituents which can be possessed.
  • Ar 11 to Ar 14 are each an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings, a structure surrounded by a, b, c and d parentheses R 1 to R 4 may be independently substituted with a benzene ring surrounded by a broken line, or may be substituted with a ring other than the benzene ring surrounded by a broken line.
  • a preferred range of Ar 11 ⁇ Ar 14 in the general formula (4) is the same as the preferred ranges of Ar 11 ⁇ Ar 14 in the general formula (3).
  • a preferred range of R 1 ⁇ R 4 in the general formula (4) are the same as the preferred ranges of R 1 ⁇ R 4 in the formula (3).
  • Preferred ranges of a and b in the general formula (4) are the same as the preferred ranges of a and b in the general formula (3).
  • the preferable ranges of c and d in the general formula (4) are the same as the preferable ranges of c and d in the general formula (3).
  • the preferable ranges of e, f, g and h in the general formula (4) are the same as the preferable ranges of e, f, g and h in the general formula (3).
  • L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom, preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent, and is preferably an alkylene group which may have a substituent. More preferably an alkylene group having 1 to 5 carbon atoms which may have a substituent, particularly preferably an alkylene group having 1 to 3 carbon atoms which may have a substituent. An ethylene group which may have a group is particularly preferable.
  • R 5 to R 8 represent an alkylene group which may have a substituent, the substituent is not particularly limited.
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond, preferably an ester bond, a thioester bond or an amide bond, and preferably an ester bond. Is more preferable.
  • the ester bond is —C ( ⁇ O) —O— or —O—C ( ⁇ O) — from the carbon atom side on which R 9 to R 12 are substituted.
  • —C ( ⁇ O) —O— is preferable.
  • R 9 to R 12 each independently represents a hydrogen atom or a methyl group, and is preferably a hydrogen atom.
  • the condensed ring-containing compound represented by the general formula (1) is preferably represented by the following general formula (5).
  • Ar 11 and Ar 12 each independently represent an aryl group or a heteroaryl group containing a benzene ring surrounded by a broken line.
  • Ar 13 and Ar 14 each independently represent an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line, and at least one of Ar 13 and Ar 14 represents a benzene ring surrounded by a broken line as one of the condensed rings.
  • An aromatic condensed ring group contained as L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • R 9 to R 12 each independently represents a hydrogen atom or a methyl group.
  • a and b each independently represents an integer of 1 to 5
  • c and d each independently represents an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent, e, f, g and h each independently represent an integer of 0 or more, and the upper limit values of e and f are 5-a and 5-b, respectively.
  • the upper limit values of g and h are values obtained by subtracting c or d from the number of substituents that Ar 13 and Ar 14 can have, respectively.
  • Ar 11 to Ar 14 are each an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings, a structure surrounded by a, b, c and d parentheses R 1 to R 4 may be independently substituted with a benzene ring surrounded by a broken line, or may be substituted with a ring other than the benzene ring surrounded by a broken line.
  • the preferred range of Ar 11 and Ar 12 in the general formula (5) is the same as the preferred ranges of Ar 11 and Ar 12 in the general formula (3).
  • a preferred range of Ar 13 and Ar 14 in the formula (5) is the same as the preferred ranges of Ar 13 and Ar 14 in the general formula (3).
  • both Ar 11 and Ar 12 represent an aromatic hydrocarbon group having 10 carbon atoms
  • both Ar 13 and Ar 14 in the general formula (5) are carbon (including a benzene ring surrounded by a broken line). More preferably, it represents an aromatic hydrocarbon group of several tens.
  • a preferred range of R 1 ⁇ R 12 in the general formula (5) are the same as the preferred ranges of R 1 ⁇ R 12 in the general formula (3).
  • the preferred range of L 1 to L 8 in the general formula (5) is the same as the preferred range of L 1 to L 4 in the general formula (4).
  • the preferable ranges of a and b in the general formula (5) are the same as the preferable ranges of a and b in the general formula (3).
  • Preferred ranges of c and d in the general formula (5) are the same as the preferred ranges of c and d in the general formula (3).
  • Preferred ranges of e, f, g and h in the general formula (5) are the same as the preferred ranges of e, f, g and h in the general formula (3).
  • the condensed ring-containing compound represented by the general formula (5) is preferably represented by any one of the following general formulas (6) to (9).
  • General formula (6) General formula (7)
  • General formula (8) General formula (9)
  • Ar 11 and Ar 12 each independently represent an aryl group or heteroaryl group containing a benzene ring surrounded by a broken line.
  • L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • R 9 to R 12 each independently represents a hydrogen atom or a methyl group.
  • a and b each independently represents an integer of 1 to 5
  • c and d each independently represents an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent, and e, f, g and h each independently represent an integer of 0 or more.
  • Ar 11 and Ar 12 are each an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings, a structure surrounded by a and b parentheses and R 1 and R 2 may be independently substituted with a benzene ring surrounded by a broken line, or may be substituted with a ring other than the benzene ring surrounded by a broken line.
  • the a, b, c, and d parenthesized structures substituted on the naphthalene ring and R 1 to R 4 may be substituted with any of the two benzene rings constituting the naphthalene ring.
  • R 3 in the general formula (6) may be substituted with a benzene ring adjacent to the 5-membered ring or may be substituted with a benzene ring not adjacent to the 5-membered ring.
  • a preferred range of the general formula (6) ⁇ Ar 11 and Ar 12 in (9) is the same as the preferred ranges of Ar 11 and Ar 12 in the general formula (5).
  • both Ar 11 and Ar 12 represent an aromatic hydrocarbon group having 6 carbon atoms (including a benzene ring surrounded by a broken line).
  • a preferred range of R 1 - R 12 in the general formula (6) to (9) are the same as the preferred ranges of R 1 - R 12 in the general formula (5).
  • the preferred range of L 1 to L 8 in the general formulas (6) to (9) is the same as the preferred range of L 1 to L 4 in the general formula (5).
  • the preferred ranges of a and b in the general formulas (6) to (9) are the same as the preferred ranges of a and b in the general formula (5).
  • Preferred ranges of c and d in the general formulas (6) to (9) are the same as the preferred ranges of c and d in the general formula (5).
  • the preferred ranges of e, f, g and h in the general formulas (6) to (9) are the same as the preferred ranges of e, f, g and h in the general formula (5).
  • L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 5 to R 8 each independently represents a single bond.
  • an alkylene group which may have a substituent L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • R 9 to R 12 each independently represent a hydrogen atom or Represents a methyl group.
  • a and b each independently represents an integer of 1 to 5
  • c and d each independently represents an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent
  • e, f, g and h each independently represent an integer of 0 or more.
  • R 1 to R 12 in the general formulas (6A), (7A), (8A) and (9A) are R in the general formulas (6), (7), (8) and (9), respectively. 1 are the same as the preferred ranges of ⁇ R 12.
  • the preferred range of L 1 to L 8 in the general formulas (6A), (7A), (8A) and (9A) is the same as the preferred range of L 1 to L 4 in the general formulas (6) to (9). It is.
  • the preferred ranges of a and b in the general formulas (6A), (7A), (8A) and (9A) are the same as the preferred ranges of a and b in the general formulas (6) to (9).
  • the preferred ranges of c and d in the general formulas (6A), (7A), (8A) and (9A) are the same as the preferred ranges of c and d in the general formulas (6) to (9).
  • the preferred ranges of e, f, g and h in the general formulas (6A), (7A), (8A) and (9A) are those of e, f, g and h in the general formulas (6) to (9). This is the same as the preferred range.
  • Ar 11 and Ar 12 represents an aryl group or a heteroaryl group containing a benzene ring surrounded by the broken line independently, Ar 11 and Ar At least one of 12 is an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings.
  • L 1 to L 4 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 5 to R 8 each independently represents a single bond or an alkylene group which may have a substituent
  • L 5 to L 8 each independently represents a single bond, an ester bond, a thioester bond or an amide bond
  • R 9 to R 12 each independently represents a hydrogen atom or a methyl group.
  • a and b each independently represents an integer of 1 to 5
  • c and d each independently represents an integer of 0 to 5.
  • R 1 to R 4 each independently represents a substituent
  • e, f, g and h each independently represent an integer of 0 or more.
  • Ar 11 and Ar 12 are each an aromatic condensed ring group containing a benzene ring surrounded by a broken line as one of the condensed rings, a structure surrounded by a and b parentheses and R 1 and R 2 may be independently substituted with a benzene ring surrounded by a broken line, or may be substituted with a ring other than the benzene ring surrounded by a broken line.
  • R 1 to R 12 in the general formulas (6A), (7A), (8A) and (9A) are R in the general formulas (6), (7), (8) and (9), respectively. 1 are the same as the preferred ranges of ⁇ R 12.
  • the preferred range of L 1 to L 8 in the general formulas (6A), (7A), (8A) and (9A) is the same as the preferred range of L 1 to L 4 in the general formulas (6) to (9). It is.
  • the preferred ranges of a and b in the general formulas (6A), (7A), (8A) and (9A) are the same as the preferred ranges of a and b in the general formulas (6) to (9).
  • the preferred ranges of c and d in the general formulas (6A), (7A), (8A) and (9A) are the same as the preferred ranges of c and d in the general formulas (6) to (9).
  • the preferred ranges of e, f, g and h in the general formulas (6A), (7A), (8A) and (9A) are those of e, f, g and h in the general formulas (6) to (9). This is the same as the preferred range.
  • the condensed ring-containing compound represented by the general formula (6) is preferably represented by the general formula (6A) or (6B), and more preferably represented by (6A).
  • the condensed ring-containing compound represented by the general formula (7) is preferably represented by the general formula (7A) or (7B), and more preferably represented by (7B).
  • the condensed ring-containing compound represented by the general formula (8) is preferably represented by the general formula (8A) or (8B), and more preferably represented by (8A).
  • the condensed ring-containing compound represented by the general formula (9) is preferably represented by the general formula (9A) or (9B), and more preferably represented by (9A).
  • the condensed ring-containing compounds represented by the general formulas (6) to (9) are represented by the general formulas (6A), (7A), (8A), (9A), (6B), (7B), (8B).
  • (9B) are preferable from the viewpoint of improving lens moldability, and the refractive index is represented by the general formula (6A), (6B), (7B), (8B) or (9B). It is more preferable from the viewpoint of making the Abbe number smaller by making it larger, and that represented by the general formula (6B), (7B), (8B), or (9B) particularly increases the refractive index and particularly increases the Abbe number This is particularly preferable from the viewpoint of reducing the size.
  • the condensed ring-containing compound represented by the general formula (1) is preferably any one of the following Xa-4 to Xa-15.
  • the molecular weight of the condensed ring-containing compound represented by the general formula (1) preferably used in the present invention is preferably 400 to 1000, more preferably 400 to 700, and particularly preferably 500 to 650. preferable.
  • the production method of the condensed ring-containing compound represented by the general formula (1) is not particularly limited and can be synthesized by a known method. For example, it can be synthesized by the method described in JP2011-68624A.
  • the cured resin composition preferably contains 40 to 85% by mass, preferably 50 to 85% by mass, of the condensed ring-containing compound represented by the general formula (1) with respect to the total amount of the cured resin composition.
  • the content is more preferably 60 to 75% by mass.
  • the cured resin composition of the present invention contains a non-conjugated vinylidene group-containing compound represented by the following general formula (2).
  • R 21 to R 26 each independently represents a substituent, and at least one of R 21 to R 26 forms a ring, or at least two of them combine with each other to form a ring. is doing.
  • the non-conjugated vinylidene group-containing compound represented by the general formula (2) does not contain a (meth) acrylate monomer.
  • the viscosity of the semi-cured product after light or heat polymerization is set within a specific range. It is possible to control and improve the heat resistance and the yield rate of the cured product obtained by thermal polymerization of the semi-cured product in the method for producing a cured product of the present invention described later.
  • R 21 to R 26 are not particularly limited, and for example, the following substituents can be used. Hydrogen atom, halogen atom, halogenated alkyl group, alkyl group, alkenyl group, acyl group, hydroxyl group, hydroxyalkyl group, aromatic ring group, heteroaromatic ring group, alicyclic group.
  • R 21 to R 26 are preferably each independently a substituent consisting of only a hydrogen atom, an oxygen atom and a carbon atom, and more preferably a substituent consisting of only a hydrogen atom and a carbon atom.
  • R 21 to R 26 are preferably a hydrogen atom, an alkyl group, or an alkenyl group, and are a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. Is more preferable.
  • group (atomic group) in this specification the description which does not describe substitution and non-substitution includes what has a substituent with what does not have a substituent.
  • the “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • the ring formed by R 21 to R 26 may be an aromatic ring, a heteroaromatic ring, or a non-aromatic ring.
  • the ring formed by R 21 to R 26 is preferably a non-aromatic ring, and more preferably a non-aromatic hydrocarbon ring.
  • the ring formed by R 21 to R 26 may further have a substituent, and examples of the substituent are preferably an alkyl group having 1 to 5 carbon atoms, a methyl group, An ethyl group, an n-propyl group, and an isopropyl group are more preferable.
  • the substituents may be bonded to form a condensed ring.
  • R 21 to R 26 may form one ring or plural rings. Further, when there are a plurality of rings formed by R 21 to R 26 , whether they are a plurality of independent rings or a condensed ring in which a plurality of independent rings are condensed with each other, as described above When one ring further has a substituent, it may be a condensed ring in which the substituents are bonded.
  • the ring formed by R 21 to R 26 is more preferably a condensed ring in which a plurality of rings are condensed, and when one ring further has a substituent, a condensed ring in which the substituents are bonded to each other It is particularly preferred that In the present specification, an embodiment in which two rings are spiro-condensed as in the specific compound described below is also included in the condensed ring.
  • one carbon atom is preferably an asymmetric carbon atom.
  • the non-conjugated vinylidene group-containing compound represented by the general formula (2) preferably includes a condensed ring in which 2 to 5 rings are condensed, and includes a condensed ring in which 2 or 3 rings are condensed. Is more preferable.
  • the number of members of each ring constituting the condensed ring is preferably 3 to 10, more preferably 3 to 9, and particularly preferably 4 to 9.
  • the non-conjugated vinylidene group-containing compound is preferably a case where (B) at least two of R 21 to R 26 are bonded to each other to form a ring.
  • a more preferable embodiment of the non-conjugated vinylidene group-containing compound will be described separately in the case of (A) and the case of (B).
  • R 21 ⁇ any two or R 24 ⁇ R 26 of R 23 are bonded to each other to form a ring, this time
  • R 21 ⁇ Any two of R 23 or any two of R 24 to R 26 that are not bonded to each other to form a ring are preferably hydrogen atoms (for example, any one of R 21 to R 23 When two are bonded to each other to form a ring, R 24 to R 26 are preferably all hydrogen atoms).
  • the non-conjugated vinylidene group-containing compound is preferably represented by the following general formula (2 ′).
  • R 21 , R 22 , R 25 and R 26 each independently represents a substituent, and A represents an atomic group necessary for forming a cyclic structure.
  • R 21 , R 22 , R 25 and R 26 are the same as the preferred ranges of R 21 to R 26 in the general formula (2).
  • R 21 , R 22 , R 25 and R 26 may further be bonded to each other to form a ring, and the ring may further have a substituent.
  • at least one of the two substituents is a hydrogen atom in only one of the pair of R 21 and R 22 or the pair of R 25 and R 26 . More preferably, both of the two substituents are hydrogen atoms.
  • R 21 and R 22 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and it is preferable that the hydrocarbon group having 1 to 5 carbon atoms does not form a ring. It is preferable that only one of R 21 and R 22 represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and the hydrocarbon group having 1 to 5 carbon atoms does not form a ring.
  • A represents an atomic group necessary for forming a cyclic structure, and the cyclic structure is not particularly limited and may be a known cyclic structure.
  • Examples of the cyclic structure include alicyclic rings (non-aromatic hydrocarbon rings), aromatic rings, heterocyclic rings, and lactone rings including —CO—.
  • A is an atomic group necessary for forming an alicyclic group having 4 to 10 carbon atoms including a carbon atom linked to A in the general formula (2) and a carbon atom constituting a non-conjugated vinylidene group. It is preferably an atomic group necessary for forming an alicyclic ring having 5 to 9 carbon atoms including a carbon atom linked to A in the general formula (2) and a carbon atom constituting a non-conjugated vinylidene group. It is particularly preferred.
  • This alicyclic ring may have a further substituent, and the preferable substituent is the same as the range of the further substituent which the ring formed by R 21 , R 22 , R 25 and R 26 may have. It is.
  • A may be an unsaturated alicyclic ring or a saturated alicyclic ring, but at least one non-conjugated vinylidene group-containing compound represented by the general formula (2) may be used as a whole. It preferably has a saturated bond.
  • A may further form a condensed ring with the substituent represented by R 21 , R 22 , R 25 and R 26 .
  • R 21 , R 22 , R 25 and R 26 each independently represent a substituent consisting of only a hydrogen atom and a carbon atom; A hydrocarbon) structure is particularly preferred.
  • the non-conjugated vinylidene group-containing compound represented by the general formula (2) has another alkenyl group in addition to the vinylidene group (non-conjugated vinylidene group).
  • the non-conjugated vinylidene group-containing compound represented by the general formula (2) a vinylidene group other than the non-conjugated vinylidene group is located in the ring formed by the R 21 , R 22 , R 25 and R 26. Is preferred.
  • the ring formed by R 21 , R 22 , R 25 and R 26 particularly preferably contains at least one unsaturated hydrocarbon ring, and is an unsaturated hydrocarbon having only one at least one double bond. It is more particularly preferable to include a ring.
  • non-conjugated vinylidene group-containing compound represented by the general formula (2) preferably used in the present invention will be listed, but the present invention is not limited to the following compounds.
  • the molecular weight of the non-conjugated vinylidene group-containing compound represented by the general formula (2) is preferably 100 to 400, more preferably 120 to 350, and particularly preferably 130 to 300.
  • ⁇ -caryophyllene that can be preferably used in the present invention is synthesized by J. Org. Am. Chem. Soc. 85, 362 (1964), Tetrahedron Lette. , 24, 1885 (1983).
  • the cured resin composition preferably contains 0.5 to 30% by mass of the non-conjugated vinylidene group-containing compound represented by the general formula (2) with respect to the total amount of the cured resin composition. More preferably, it is contained in an amount of 2 to 20% by mass.
  • the cured resin composition of the present invention contains 2 to 50% by mass of the non-conjugated vinylidene group-containing compound represented by the general formula (2) with respect to the condensed ring-containing compound represented by the general formula (1).
  • the content is preferably 2 to 35% by mass, more preferably 2 to 20% by mass.
  • the curable resin composition of the present invention preferably contains a radical photopolymerization initiator.
  • a radical photopolymerization initiator There is no restriction
  • the photo radical polymerization initiator specifically, the following compounds can be used.
  • Irgacure 184 (1-hydroxycyclohexyl phenyl ketone), 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-2, manufactured by BASF Corporation.
  • the amount of the radical photopolymerization initiator added to the cured resin composition is not particularly limited, but is preferably 0.01 to 5% by mass relative to the total amount of the cured resin composition. It is more preferably from 05 to 1.0% by mass, particularly preferably from 0.05 to 0.5% by mass.
  • the curable resin composition of the present invention preferably contains a thermal radical polymerization initiator.
  • a thermal radical polymerization initiator By adding such a thermal radical polymerization initiator to the cured resin composition in advance, the semi-cured product of the present invention can be easily converted into a cured product of the present invention having high heat resistance by thermal polymerization with good moldability. It can be manufactured with high productivity.
  • thermal radical polymerization initiator specifically, the following compounds can be used. 1,1-di (t-hexylperoxy) cyclohexane, 1,1-di (t-butylperoxy) cyclohexane, 2,2-di (4,4-di- (t-butylperoxy) cyclohexyl) propane, t- Hexyl peroxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, dicumyl peroxide, di-t-butyl peroxide, t-butylperoxy-2-ethylhexano Ate, t-hexylperoxy-2-ethylhexanoate, cumene hydroperoxide, t-butyl hydroperoxide, 2,3-dimethyl-2,3-diphenylbutane.
  • a hydroperoxide thermal radical polymerization initiator having a hydroperoxide group in the molecule as the thermal radical polymerization initiator, and further, a hydroperoxide having a hydroperoxide group in the molecule. It is more preferable to use at least one type of thermal radical polymerization initiator and a non-hydroperoxide thermal radical polymerization initiator having no hydroperoxide group in the molecule.
  • non-hydroperoxide thermal radical polymerization initiator perfoil O (t-butylperoxy-2-ethylhexanoate) manufactured by NOF Corporation and the hydroperoxide thermal radical polymerization initiator are used.
  • Park Mill H cumene hydroperoxide manufactured by Nippon Oil & Fats Co., Ltd. can be preferably used.
  • hydroperoxide thermal radical polymerization initiator having a hydroperoxide group in the molecule is that the hydroperoxide thermal radical polymerization initiator is a polymer of a non-conjugated vinylidene group-containing compound monomer. This is because there is an effect of promoting chain transfer in the interior, the controllability of the three-dimensional structure is further improved, and the deformability of the semi-cured product can be imparted.
  • the hydroperoxide thermal radical polymerization initiator is more preferably used in combination with a non-hydroperoxide thermal radical polymerization initiator having a low thermal polymerization initiation temperature.
  • the addition amount of the thermal radical polymerization initiator in the cured resin composition is not particularly limited, but the condensed ring-containing compound represented by the general formula (1) and the non-conjugated compound represented by the general formula (2)
  • the content is preferably from 0.01 to 5.0% by mass, preferably from 0.1 to 4.0% by mass, based on the total of the vinylidene group-containing compound and the polymer having a polymerizable group described later in the side chain. Is more preferable, and 0.3 to 3.0% by mass is particularly preferable.
  • the cured resin composition of the present invention may contain other monomers other than the condensed ring-containing compound represented by the general formula (1), as long as it does not contradict the gist of the present invention. It is preferable to include an acrylate monomer.
  • the monofunctional (meth) acrylate monomer used in the present invention for example, the following can be used.
  • Adamantyl (meth) acrylates such as 1-adamantyl (meth) acrylate, norbornyl (meth) acrylates such as isobornyl (meth) acrylate, tricyclo [5,2,1,0 2,6] dec-8-yl acrylate, etc.
  • Tricyclodecane (meth) acrylates 2-ethyl-2-butylpropanediol (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylhexyl carbitol (meth) acrylate, 2-hydroxybutyl (meth) acrylate 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, (Meth) acrylate, 1- or 2-naphthyl (meth) acrylate, butanediol mono (meth) acrylate, butoxyethyl (meth) acrylate, butyl (meth) acrylate, cetyl (meth) acrylate, EO-modified cresol (meth) Acrylate, diprop
  • the curable resin composition of the present invention preferably includes a monofunctional (meth) acrylate monomer having an aromatic ring among monofunctional (meth) acrylate monomers.
  • a monofunctional (meth) acrylate monomer having an aromatic ring used in the present invention, for example, the following are preferably used.
  • benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, O-phenylphenol (meth) acrylate, and O-phenylphenol EO modified (meth) acrylate are more preferable, and benzyl (meth) acrylate and phenoxyethyl (meth) acrylate are preferred.
  • benzyl acrylate and phenoxyethyl acrylate are more particularly preferred.
  • the cured resin composition of the present invention contains a monofunctional (meth) acrylate monomer, and the monofunctional (meth) acrylate monomer is 10 to 80% by mass with respect to the condensed ring-containing compound represented by the general formula (1). It is preferably contained, more preferably 10 to 70% by mass, and particularly preferably 15 to 65% by mass.
  • the cured resin composition may contain additives such as a polymer, other monomers, a dispersant, a plasticizer, a heat stabilizer, and a release agent, as long as the gist of the present invention is not violated.
  • additives such as a polymer, other monomers, a dispersant, a plasticizer, a heat stabilizer, and a release agent, as long as the gist of the present invention is not violated.
  • non- (meth) acrylic monomers may be included as other monomer components.
  • the addition amount of the non- (meth) acrylic monomer is preferably 0 to 20% by mass, and preferably 0 to 15% by mass in the total monomers.
  • the non- (meth) acrylic monomer is not particularly limited, and for example, the following compounds may be used.
  • fill the conditions of this invention may be included.
  • the polymer having a polymerizable group in the side chain may be a homopolymer or a copolymer, and in the case of being a copolymer, at least one copolymer component has a polymerizable group side. What is necessary is just to have in a chain
  • Ra and Rb each independently represent hydrogen or an alkyl group.
  • the molecular weight of the polymer having a polymerizable group in the side chain is preferably 1,000 to 10,000,000, more preferably 5,000 to 300,000, and particularly preferably 10,000 to 200,000.
  • the glass transition temperature (hereinafter also referred to as Tg) of the polymer having a polymerizable group in the side chain is preferably 50 to 400 ° C, more preferably 70 to 350 ° C, and more preferably 100 to 300 ° C. It is particularly preferred.
  • the method for producing a semi-cured product of the present invention includes a step of curing the cured resin composition of the present invention.
  • Examples of the step of curing the cured resin composition of the present invention include light irradiation and heating. It is preferable that the manufacturing method of the semi-hardened
  • at least one of light irradiation and heating is performed on the cured resin composition of the present invention, and a complex viscosity at 25 ° C. and a frequency of 10 Hz is 10 5 to 10 8 mPa ⁇ s.
  • the cured resin composition of the present invention is preferably irradiated with light to form a semi-cured product having a complex viscosity of 10 5 to 10 8 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz. More preferably.
  • the said radical polymerization initiator contains a radical photopolymerization initiator further.
  • the “semi-cured product” is a product obtained by polymerizing a cured resin composition, which is not completely solid and has a certain degree of fluidity.
  • the light and / or heated polymer of the cured resin composition having a complex viscosity of 10 5 to 10 8 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz is a semi-cured product.
  • the thing of 1.0x10 ⁇ 9 > mPa * s is considered as a semi-hardened
  • the “cured product” means a product obtained by polymerizing a cured resin composition and in a completely solid state.
  • the present invention will be specifically described with reference to preferred embodiments of the method for producing a semi-cured product of the present invention and the method for producing a cured product of the present invention.
  • cured material of this invention includes the manufacturing method of the semi-hardened material of this invention, it describes in the manufacturing method column of the semi-hardened material of this invention about the preferable aspect of the manufacturing method common to both.
  • the cured resin composition is irradiated with light and / or heated to have a complex viscosity of 10 5 to 10 8 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz. It is preferable to include the process of obtaining.
  • the cured resin composition may be directly placed on a mold used for thermal polymerization in the method for producing a cured product of the present invention described later before light irradiation and / or heating.
  • the cured resin composition When the cured resin composition is irradiated with light and / or heated, it is placed in a mold different from the mold and a semi-cured product is produced, and then the light-cured product obtained in the method for producing a cured product of the present invention described later is used. You may move a semi-hardened
  • the mold can be heated while combining the two molds while pressurizing the contents.
  • a low-viscosity composition is injected into the mold, leakage into the mold clearance will occur.
  • the cured resin composition used in the method for producing a semi-cured product of the present invention generally has a low viscosity for direct injection into a mold.
  • the polymer having a polymerizable group in the side chain is further added to adjust the viscosity of the cured resin composition, and It is also preferable from the viewpoint of manufacturability to obtain a cured product by performing semi-curing by light irradiation and / or heating and thermal polymerization described later in one mold.
  • the semi-cured product is produced.
  • the semi-cured product is produced.
  • a so-called preform mold when using a mold different from the mold, it is preferable to use a so-called preform mold.
  • the preform mold may be made of metal, glass, or resin. Considering repeated use in the mass production process, the preform mold is preferably made of metal or glass.
  • the semi-cured product of the present invention when used as a lens, it is preferable that at least one surface of the preform mold has the same shape as or close to that of the mold, and the mold shape is formed on both surfaces. It is more preferable that they have the same or similar shape.
  • Light irradiation conditions Preferred conditions for light irradiation in the method for producing a semi-cured product of the present invention will be described below.
  • the light irradiation is preferably performed so that the complex viscosity of the semi-cured product after the light irradiation at 25 ° C. and a frequency of 10 Hz is 10 5 to 10 8 mPa ⁇ s, 10 5 to 10 7.5 mPa ⁇ s. It is more preferable to carry out so that the pressure is 10 5.5 to 10 7.5 mPa ⁇ s.
  • the light used for the light irradiation is preferably ultraviolet light or visible light, and more preferably ultraviolet light.
  • a metal halide lamp, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a sterilization lamp, a xenon lamp, an LED light source lamp, or the like is preferably used.
  • the atmosphere at the time of the light irradiation is preferably air or inert gas substitution, and more preferably nitrogen atmosphere until the oxygen concentration becomes 1% or less.
  • the preferable conditions for heat semi-curing in the method for producing a semi-cured product of the present invention will be described below.
  • the semi-cured product of the present invention is produced by the method for producing a semi-cured product of the present invention.
  • a semi-cured product can be preferably used in the method for producing a cured product of the present invention described later.
  • the preferable range of the complex viscosity of the semi-cured product of the present invention is the same as the preferable range of the complex viscosity of the semi-cured product in the above-described method for producing a semi-cured product of the present invention.
  • the radical photopolymerization initiator is completely consumed and may not be contained at all, or the radical photopolymerization initiator may remain.
  • the glass transition temperature (hereinafter also referred to as Tg) of the semi-cured product of the present invention is preferably ⁇ 150 to 0 ° C., more preferably ⁇ 50 to 0 ° C., and ⁇ 20 to 0 ° C. Is particularly preferred.
  • cured material of this invention includes the thermal-polymerization process of putting the semi-hardened
  • cured material of this invention performs at least one among light irradiation and a heating with respect to the cured resin composition containing a (meth) acrylate monomer, a nonconjugated vinylidene group containing compound, and a thermal radical polymerization initiator.
  • the said radical polymerization initiator may contain the radical photopolymerization initiator further.
  • cured material of this invention includes the process of light-irradiating with respect to the said cured resin composition, It is preferable that the said radical polymerization initiator is a radical photopolymerization initiator.
  • thermoforming mold The mold used in the method for producing a cured product of the present invention is also referred to as a thermoforming mold.
  • the thermoforming mold has a configuration in which two molds can be combined and heated while pressing the contents.
  • die As such a thermoforming mold, for example, the one described in JP2009-126011A can be used.
  • the semi-cured product produced by the method for producing a semi-cured product of the present invention is placed in a mold.
  • the process of putting a semi-cured product into a mold will be described.
  • the semi-cured product after light irradiation and / or heating is directly placed on a thermoforming mold and irradiated with light and / or heated as described in the above-described method for producing a semi-cured product of the present invention, or The light is irradiated and / or heated in a separate mold from the thermoforming mold.
  • thermoforming mold When the semi-cured product after the light irradiation is directly placed on the thermoforming mold and irradiated with light and / or heated, there is no need for the operation to put it in the thermoforming mold, and it is put in the mold for explanation. It is only described.
  • the light-cured and / or heated semi-cured product when placed in a mold different from the thermoforming mold and irradiated and / or heated, it means a step of moving to the thermoforming mold. .
  • a method of moving the semi-cured product after the light irradiation and / or heating to the thermoforming mold for example, a syringe, an air tweezer having a vacuum pad and a vacuum generator can be used. Since the semi-cured product of the present invention has a complex viscosity within a specific range, it can be easily moved to a thermoforming mold using air tweezers or the like.
  • molding die is pressure-deformed, it heats and heat-polymerizes, and hardened
  • the pressure deformation and the heating may be performed at the same time, the heating may be performed after the pressure deformation, or the pressure deformation may be performed after the heating. It is preferable to carry out simultaneously. Further, it is also preferable that the pressure deformation and the heating are performed at the same time and the heating is further performed at a higher temperature after the pressure is stabilized.
  • the pressure in the pressure deformation is preferably 1 kg / cm 2 to 100 kg / cm 2 , more preferably 3 kg / cm 2 to 50 kg / cm 2 , and 3 kg / cm 2 to 30 kg / cm 2 . It is particularly preferred.
  • the heating temperature is preferably 80 to 300 ° C., more preferably 120 to 300 ° C., and particularly preferably 150 to 280 ° C., which is performed simultaneously with the pressure deformation. On the other hand, even when heated to a higher temperature after the pressure is stabilized, the temperature is preferably 80 to 300 ° C, more preferably 120 to 300 ° C, and particularly preferably 150 to 280 ° C.
  • the thermal polymerization time is preferably 30 to 1000 seconds, more preferably 30 to 500 seconds, and particularly preferably 60 to 300 seconds.
  • the atmosphere at the time of the thermal polymerization is preferably air or inert gas substitution, and more preferably nitrogen atmosphere until the oxygen concentration becomes 1% or less.
  • the cured product of the present invention is produced by the method for producing a cured product of the present invention.
  • preferable characteristics of the cured product of the present invention will be described.
  • the cured product of the present invention preferably has a high refractive index from the viewpoint of use for lenses and the like among optical component applications.
  • the cured product of the present invention preferably has a refractive index nD at a wavelength of 589 nm of 1.45 or more, more preferably 1.61 or more, more preferably 1.62 or more, and 1.63. It is even more particularly preferable that it is above, and it is most preferable that it is 1.65 or more.
  • the cured product of the present invention preferably has a low Abbe number from the viewpoint of reducing chromatic aberration when used for lenses and the like among optical component applications.
  • the cured product of the present invention preferably has an Abbe number of 25 or less at a wavelength of 589 nm, more preferably 24 or less, particularly preferably 23.5 or less, and particularly preferably 23 or less. Even more preferably, it is 22.5 or less, and most preferably 22 or less.
  • the Abbe number ⁇ D is calculated by the following formula (A) by measuring the respective refractive indexes nD, nF, and nC at wavelengths 589 nm, 486 nm, and 656 nm.
  • the cured product of the present invention preferably has a maximum thickness of 0.1 to 10 mm.
  • the maximum thickness is more preferably 0.1 to 5 mm, and particularly preferably 0.15 to 3 mm.
  • the cured product of the present invention preferably has a maximum diameter of 1 to 1000 mm.
  • the maximum diameter is more preferably 2 to 50 mm, and particularly preferably 2.5 to 10 mm.
  • a cured product of such a size is particularly useful for optical parts having a high refractive index.
  • Such a thick molded body is generally not easy because the solvent is difficult to escape even if it is manufactured by the solution casting method, and molding is not easy.
  • the yield is high because molding is easy and burrs are not easily generated, and complex shapes such as aspherical surfaces can be easily realized.
  • a cured product can be obtained.
  • cured material which has high heat resistance can be manufactured easily.
  • the cured product of the present invention is preferably a molded article having both high refraction, light transmittance and light weight and excellent optical properties, and the optical component of the present invention uses the cured product of the present invention.
  • the kind of the optical component of the present invention is not particularly limited. In particular, it can be suitably used as an optical component utilizing the excellent optical properties of the cured resin composition, particularly an optical component that transmits light (so-called passive optical component).
  • Examples of the optical functional device provided with such optical components include various display devices (liquid crystal display, plasma display, etc.), various projector devices (OHP, liquid crystal projector, etc.), optical fiber communication devices (optical waveguide, optical amplifier, etc.), camera, etc. And an imaging device such as a video.
  • Examples of the passive optical component used in the optical functional device include a lens, a prism, a prism sheet, a panel (plate-shaped molded body), a film, an optical waveguide (film-like or fiber-like), an optical disk, and an LED seal. Examples thereof include a stopper.
  • an optional coating layer for example, a protective layer that prevents mechanical damage to the coated surface due to friction and wear, light rays with an undesirable wavelength that causes deterioration of inorganic particles and substrates, etc.
  • a light absorbing layer that absorbs light a transmission shielding layer that suppresses or prevents the transmission of reactive low molecules such as moisture and oxygen gas, an antiglare layer, an antireflection layer, a low refractive index layer, etc.
  • a multilayer structure may be used.
  • an optional coating layer include a transparent conductive film and gas barrier film made of an inorganic oxide coating layer, a gas barrier film made of an organic coating layer, a hard coat, and the like.
  • Known coating methods such as a sputtering method, a dip coating method, and a spin coating method can be used.
  • the optical component using the cured product of the present invention is particularly suitable for a lens substrate.
  • the lens substrate produced using the cured resin composition of the present invention has a low Abbe number, and preferably has high refractive properties, light transmittance and light weight, and is excellent in optical properties.
  • the refractive index of the lens substrate can be arbitrarily adjusted by appropriately adjusting the type of monomer constituting the cured resin composition.
  • the “lens substrate” means a single member that can exhibit a lens function. A film or a member can be provided on the surface or the periphery of the lens substrate according to the use environment or application of the lens.
  • a protective film, an antireflection film, a hard coat film, or the like can be formed on the surface of the lens substrate.
  • the periphery of the lens base material can be fitted and fixed to a base material holding frame or the like.
  • these films and frames are members added to the lens base material, and are distinguished from the lens base material itself in this specification.
  • the lens substrate When the lens substrate is used as a lens, the lens substrate itself may be used alone as a lens, or may be used as a lens with a film or a frame added as described above.
  • the type and shape of the lens using the lens substrate are not particularly limited. Since the lens base material has a low Abbe number, it can be preferably used for a chromatic aberration correction lens. Is preferably used for in-vehicle and endoscope lenses.
  • the above Xa-4 was synthesized by the following method.
  • the following reaction was performed under a nitrogen stream. 10.2 g of 1-indanone and 19.4 g of o-phthalaldehyde were dissolved in 80.0 g of methanol.
  • the reaction solution was heated, and 25.8 g of potassium hydroxide was dissolved in 96.0 g of methanol and added dropwise while maintaining 60 ° C. After stirring for 3 hours, the reaction solution was returned to room temperature, and the precipitated crystals were collected by filtration to obtain 20.3 g of 2,3-benzofluorenone.
  • the above Xa-5 was synthesized by the following method.
  • the following reaction was performed under a nitrogen stream.
  • 10.0 g of dibenzo [ ⁇ , ⁇ ] fluoren-12-one and 19.7 g of phenoxyethanol were suspended in 60 g of toluene, and 0.23 g of 3-mercaptopropionic acid was added.
  • 7.7 g of sulfuric acid stirring at 120 ° C. for 27 hours, adding 20 g of methanol, stirring for 1 hour, adding 30 g of water, returning to room temperature, removing the supernatant, and purifying the residue by column chromatography.
  • the above Xa-6 to 15 were synthesized in the same manner as the above Xa-4 method.
  • the 1 H-NMR data of Xa-6, Xa-8 and Xa-10 are shown in FIGS. 3 to 5, respectively.
  • the condensed ring-containing compounds A to C were synthesized in the same manner as in the method of Xa-4.
  • Non-conjugated vinylidene group-containing compound ⁇ Non-conjugated vinylidene group-containing compound>
  • non-conjugated vinylidene group-containing compounds that can be used in Examples are described, but optical isomers need not be particularly limited and can be used.
  • B-5 Product name ⁇ -caryophyllene manufactured by Tokyo Chemical Industry Co., Ltd.
  • the cured resin composition 10 mg injected into a cylindrical transparent preform mold having a diameter of 4 mm and a height of 1.5 mm is irradiated with ultraviolet rays of 15 mW / cm 2 using Execute 3000 (manufactured by HOYA). Irradiated for the stated time to produce a semi-cured product.
  • the ceiling part of the thermoforming mold for making a lens having a diameter of 4.0 mm comprising the upper mold (ceiling part mold), the trunk mold, and the lower mold (bottom mold) was removed, and then the shape of the preform mold was obtained.
  • the semi-cured product was transferred from the preform mold to a thermoforming mold using air tweezers.
  • the temperature was raised to 200 ° C. while applying a pressure of 30 kgf / cm 2 to the semi-cured product, and then cooled to room temperature.
  • the amount of burrs generated by the resin leaking into the thermoforming mold clearance was measured as the resin leakage, and the following criteria were used: It was evaluated with.
  • X The amount of resin leakage is 0.3 mg or more, which is problematic in practical use. The obtained results are shown in Table 1 below. Note that the mold resin clearance leak evaluation differs from the conventional resin leak amount evaluation in that a process of transferring the semi-cured product from the preform mold to the thermoforming mold is added. is there.
  • ⁇ Lens moldability evaluation> The same process as the mold resin clearance leakage evaluation (ii) was repeated 10 times, and the appearance of each of the produced lenses was evaluated using a digital micro scoop (trade name: VHX-1000) manufactured by Keyence Corporation. Fine irregularities (wrinkles) on the surface of the flange portion of the lens or cracks in the lens were regarded as defective, and non-defective products were regarded as good. Ten lenses were evaluated, and the ratio of non-defective products was defined as the non-defective rate, and evaluated according to the following criteria. A: The yield rate was 85% or more. ⁇ : The yield rate was 70% or more. ⁇ : The yield rate was 30% or more. X: The yield rate was less than 30%. The obtained results are shown in Table 1 below.
  • thermo-cured product A cured resin composition injected into a transparent glass mold having a diameter of 10 mm and a thickness of 1 mm was irradiated with 15 mW / cm 2 of ultraviolet light using Execute 3000 (manufactured by HOYA) for the time indicated in the following table, and a semi-cured product was applied. Obtained. Next, the obtained semi-cured product was heated at 200 ° C. for 5 minutes using a hot plate to obtain a thermo-cured product.
  • the refractive index and Abbe number at 589 nm of the obtained thermosetting product were measured using an Abbe meter (manufactured by Atago Co., Ltd.), and the refractive index and Abbe number of the obtained cured product were obtained. The obtained results are shown in Table 1 below.
  • the cured resin composition having a diameter of 10 mm and a thickness of 1 mm sandwiched between a transparent metal plate and a metal plate in the same manner as the mold is irradiated with 15 mW / cm 2 ultraviolet rays using Execute 3000 (manufactured by HOYA).
  • the semi-cured product was obtained by irradiation for the time described in 1.
  • the obtained semi-cured product was heated at 200 ° C. for 5 minutes using a hot plate to obtain a thermo-cured product.
  • the obtained thermoset was heated in an oven at 150 ° C. for 2 hours, and the rate at which the cured product remained in the glass when the glass and the metal plate were separated was determined and evaluated according to the following criteria.
  • the cured product produced using the cured resin composition of the present invention had a low Abbe number, with the occurrence of burrs being suppressed during molding.
  • the cured product produced using the cured resin composition of Comparative Example 1 that does not contain the non-conjugated vinylidene group-containing compound represented by the general formula (2) is one in which burrs are generated during molding. there were.
  • cured material manufactured using the cured resin composition of the comparative example 2 using the condensed ring containing compound outside the range of the general formula (1) of this invention had a high Abbe number.
  • a cured product produced using the cured resin composition of Comparative Example 3 having no condensed ring and using a condensed ring-containing compound outside the range of the general formula (1) of the present invention has a high Abbe number. Met.
  • the semi-cured products produced during each evaluation using the cured resin composition of the present invention had a complex viscosity of 10 5 to 10 8 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz. It was.

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